WO2018225999A1 - 화합물 및 이를 포함하는 유기 태양 전지 - Google Patents

화합물 및 이를 포함하는 유기 태양 전지 Download PDF

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WO2018225999A1
WO2018225999A1 PCT/KR2018/006358 KR2018006358W WO2018225999A1 WO 2018225999 A1 WO2018225999 A1 WO 2018225999A1 KR 2018006358 W KR2018006358 W KR 2018006358W WO 2018225999 A1 WO2018225999 A1 WO 2018225999A1
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group
substituted
unsubstituted
same
layer
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English (en)
French (fr)
Korean (ko)
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임보규
장송림
최두환
김지훈
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주식회사 엘지화학
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Priority to US16/482,021 priority Critical patent/US20200002468A1/en
Priority to CN201880012168.0A priority patent/CN110337439B/zh
Priority to JP2019542998A priority patent/JP6873253B2/ja
Publication of WO2018225999A1 publication Critical patent/WO2018225999A1/ko

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Definitions

  • the present specification relates to a compound and an organic solar cell including the same.
  • Organic solar cells are devices that can directly convert solar energy into electrical energy by applying the photovoltaic effect.
  • Solar cells can be divided into inorganic solar cells and organic solar cells, depending on the material of the thin film.
  • Typical solar cells are made of p-n junctions by doping crystalline silicon (Si), an inorganic semiconductor. Electrons and holes generated by absorbing light diffuse to the p-n junction and are accelerated by the electric field to move to the electrode.
  • the power conversion efficiency of this process is defined as the ratio of the power given to the external circuit and the solar power entered into the solar cell, and is currently achieved by 24% when measured under standardized virtual solar irradiation conditions.
  • organic semiconductor solar cells which are easy to process, inexpensive and have various functionalities are spotlighted as long-term alternative energy sources.
  • An object of the present specification is to provide a compound and an organic solar cell including the same.
  • the present specification provides a compound including a unit of Formula 1 below.
  • p and q are the same as or different from each other, and each independently an integer of 0 to 3,
  • r and s are the same as or different from each other, and each independently an integer of 1 to 3,
  • X1 to X3 are the same as or different from each other, and each independently S, O, Se, Te, NR, CRR ', SiRR', PR or GeRR ',
  • Y1 to Y4 are the same as or different from each other, and each independently S, O, Se, Te, NR, CRR ', SiRR', PR or GeRR ',
  • R1 to R12, R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substitute
  • n is an integer from 1 to 10,000.
  • Another embodiment of the present specification is a first electrode
  • a second electrode provided to face the first electrode
  • At least one organic material layer provided between the first electrode and the second electrode, including a photoactive layer,
  • At least one layer of the organic material layer provides an organic solar cell comprising the compound.
  • Compound according to an exemplary embodiment of the present disclosure exhibits a planarity, excellent aggregation properties and crystallinity
  • Compounds according to one embodiment of the present specification may have the effect of reducing the bandgap and / or increasing the amount of light absorption. Accordingly, when applied to an organic solar cell, as the high current value Isc is exhibited, excellent efficiency can be exhibited.
  • Compound according to an exemplary embodiment of the present specification has a high solubility and at the same time have a suitable solubility, there is an economical advantage in time and / or cost in the manufacturing of the device.
  • FIG. 1 illustrates an organic solar cell according to an exemplary embodiment of the present specification.
  • 3 is a diagram showing a result of NMR measurement of Compound C.
  • 5 is a diagram showing a result of NMR measurement of Compound D.
  • FIG. 6 is a diagram illustrating photoelectric conversion characteristics of an organic solar cell according to an exemplary embodiment of the present specification.
  • An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
  • unit means a repeating structure contained in a compound. That is, the “unit” may mean a structure included in the form of two or more groups in the compound by the polymerization reaction.
  • the term "comprising a unit” means being included in a main chain in a compound.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • the term "substituted or unsubstituted” is deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl group; Alkyl groups; Cycloalkyl group; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Alkenyl groups; Silyl groups; Siloxane groups; Boron group; Amine groups; Aryl phosphine group; Phosphine oxide groups; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • the halogen group may be fluorine, chlorine, bromine or iodine.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30.
  • the amide group may be substituted with nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C30.
  • the ester group may be substituted with oxygen of the ester group having a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-o
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. It is not.
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
  • the amine group is -NH 2 ; Alkylamine group; N-arylalkylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group and the like, but is not limited thereto.
  • the N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.
  • the N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N in the amine group.
  • the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroarylamine group are substituted for N of the amine group.
  • the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthioxy group, the alkyl sulfoxy group, and the N-alkylheteroarylamine group is the same as the example of the alkyl group described above.
  • the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group
  • the alkyl sulfoxy group includes mesyl, ethyl sulfoxy, propyl sulfoxy, and butyl sulfoxy groups. Etc., but is not limited thereto.
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • the boron group may be -BR 100 R 200 , wherein R 100 and R 200 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.
  • the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group, fluorenyl group and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is the same as the examples of the aryl group described above.
  • the aryloxy group may be a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like.
  • arylthioxy group examples include a phenylthioxy group and 2- The methylphenyl thioxy group, 4-tert- butylphenyl thioxy group, etc. are mentioned,
  • An aryl sulfoxy group includes a benzene sulfoxy group, p-toluene sulfoxy group, etc., but is not limited to this.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heterocyclic group may be monocyclic or polycyclic.
  • heterocyclic group examples include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heterocyclic group described above.
  • heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heterocyclic group described above.
  • X1 to X3 are the same as or different from each other, and each independently S, O, Se, Te, NR, CRR ', SiRR', PR, or GeRR ', and R and R' are mutually different.
  • X1 to X3 are the same as or different from each other, and each independently, S, NR, or CRR ', and R and R' are as described above.
  • X1 to X3 are each S.
  • the compound is benzo [1,2-c: 4,5-c: 4,5-c '] dithiophene-4,8-dione (benzo [1,2-c: 4 A conformation lock fixed between O and Y1 (and / or Y2) of the, 5-c '] dithiophene-4,8-dione group between R11 (and / or R12) and Y3 (and / or Y4) Since the molecule exhibits planarity with)), it shows strong aggregation characteristics and improves crystallinity. In addition, the pi-pi interaction in the compound is strong, increasing charge transfer due to hopping.
  • the compound according to one embodiment of the present specification is benzo [1,2-c: 4,5-c: 4,5-c '] dithiophene-4,8 having weak electron-withdrawing properties. It contains simultaneously benzo [1,2-c: 4,5-c '] dithiophene-4,8-dione groups and benzothialdiazole groups with strong electron-withdrawing properties.
  • p and q are the same as or different from each other, and each independently an integer of 0 to 3, and when p and q are each 2 or more, the structures in parentheses are the same or different from each other.
  • p and q are the same as each other, and 0 or 1, respectively.
  • p and q are zero.
  • p and q are 1.
  • r and s are the same as or different from each other, each independently represent an integer of 1 to 3, and when r and s are each 2 or more, the structures in parentheses are the same or different from each other.
  • r and s are the same as each other, and are 1 or 2, respectively.
  • r and s are 1.
  • r and s are two.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
  • R1 to R12 and Y1 to Y4 are the same as defined in Formula 1,
  • Y3 'and Y4' are the same as or different from each other, and each independently S, O, Se, Te, NR, CRR ', SiRR', PR or GeRR ',
  • R5 ', R6', R7 ', R8', R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubsti
  • R9 and R10 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
  • R9 and R10 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group.
  • R9 and R10 are the same as or different from each other, and are each independently a linear or branched alkyl group.
  • R9 and R10 are the same as or different from each other, and each independently a branched alkyl group having 1 to 30 carbon atoms.
  • R9 and R10 are the same as or different from each other, and each independently a branched alkyl group having 1 to 15 carbon atoms.
  • R9 and R10 are 2-ethylhexyl group.
  • Chemical Formula 1 is represented by the following Chemical Formula 2.
  • Y1 to Y4 are the same as or different from each other, and each independently S, O, Se, Te, NR, CRR ', SiRR', PR or GeRR ', and R and R' are As described above.
  • Y1 to Y4 are the same as or different from each other, and are each independently S, NR, or CRR ', and R and R' are as described above.
  • Y1 to Y4 are each S.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; Halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; Halogen group; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted alkoxy group.
  • R2, R3 and R5 to R8 are hydrogen.
  • Chemical Formula 1 is any one of the following Chemical Formulas 2-1 to 2-4.
  • R1, R4, R11, R12 and n are the same as defined in the formula (1).
  • R1 and R4 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.
  • R1 and R4 are the same as or different from each other, and each independently hydrogen; Or a linear or branched alkyl group.
  • R1 and R4 are the same as or different from each other, and each independently hydrogen; Or a branched alkyl group having 1 to 30 carbon atoms.
  • R1 and R4 are each hydrogen.
  • R1 and R4 are 2-octyldodecane groups, respectively.
  • R11 and R12 are the same as or different from each other, and each independently hydrogen; Halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • R11 and R12 are the same as or different from each other, and each independently hydrogen; Halogen group; Or a substituted or unsubstituted alkoxy group.
  • R11 and R12 are the same as or different from each other, and are each independently a halogen group.
  • R11 and R12 are each fluorine.
  • R11 is fluorine and R12 is hydrogen.
  • R11 and R12 are the same as or different from each other, and are each independently a substituted or unsubstituted alkoxy group.
  • R11 and R12 are the same as or different from each other, and are each independently an alkoxy group having 1 to 30 carbon atoms.
  • R11 and R12 are the same as or different from each other, and are each independently an alkoxy group having 1 to 15 carbon atoms.
  • Chemical Formula 1 is represented by any one of the following compounds.
  • n is an integer from 1 to 10,000.
  • the terminal group of the compound is a substituted or unsubstituted aryl group.
  • the terminal group of the compound is benzotrifluoride.
  • a second electrode provided to face the first electrode
  • It includes at least one organic material layer provided between the first electrode and the second electrode, including a photoactive layer,
  • At least one layer of the organic material layer provides an organic solar cell comprising the compound.
  • the organic solar cell may further include an additional organic material layer.
  • the organic solar cell may reduce the number of organic material layers by using an organic material having several functions at the same time.
  • the organic solar cell includes a first electrode, a photoactive layer, and a second electrode.
  • the organic solar cell may further include a substrate, a hole transport layer, and / or an electron transport layer.
  • FIG. 1 illustrates an organic solar cell according to an exemplary embodiment of the present specification. Specifically, FIG. 1 illustrates an organic solar cell in which a substrate, a first electrode, a hole transport layer, a photoactive layer, and a second electrode are sequentially stacked.
  • the photoactive layer includes the compound.
  • the organic material layer includes a hole transport layer, a hole injection layer, or a layer for simultaneously transporting holes and holes, and the hole transport layer, the hole injection layer, or the layer for simultaneously transporting holes and holes is It includes the compound.
  • the organic material layer includes an electron injection layer, an electron transport layer, or a layer for simultaneously injecting and transporting electrons, and the electron injection layer, the electron transport layer, or the layer for simultaneously transporting electrons and transporting electrons. It includes the compound.
  • the first electrode is an anode
  • the second electrode is a cathode.
  • the first electrode is a cathode
  • the second electrode is an anode.
  • the organic solar cell may be arranged in the order of cathode, photoactive layer and anode, and may be arranged in the order of anode, photoactive layer and cathode, but is not limited thereto.
  • the organic solar cell may be arranged in order of an anode, a hole transport layer, a photoactive layer, an electron transport layer, and a cathode, or may be arranged in the order of a cathode, an electron transport layer, a photoactive layer, a hole transport layer, and an anode. It is not limited to this.
  • the photoactive layer includes an electron donor and an acceptor, and the electron donor includes the compound.
  • the electron acceptor material may be selected from the group consisting of fullerenes, fullerene derivatives, vasocuprones, semiconducting elements, semiconducting compounds, and combinations thereof.
  • the electron acceptor may be PC 60 BM (phenyl C 60 -butyric acid methyl ester), PC 61 BM (phenyl C 61 -butyric acid methyl ester) or PC 71 BM (phenyl C 71 -butyric acid methyl ester).
  • PC 60 BM phenyl C 60 -butyric acid methyl ester
  • PC 61 BM phenyl C 61 -butyric acid methyl ester
  • PC 71 BM phenyl C 71 -butyric acid methyl ester
  • the electron donor and the electron acceptor constitute a bulk hetero junction (BHJ).
  • the electron donor material and the electron acceptor material may be mixed in a ratio (w / w) of 1:10 to 10: 1.
  • the electron donor material and the electron acceptor material may be mixed in a ratio (w / w) of 1: 1 to 1:10, and more specifically, the electron donor material and the electron acceptor material may be 1: 1 to 1: 5.
  • the photoactive layer has a bilayer structure including a n-type organic compound layer and a p-type organic compound layer, and the p-type organic compound layer includes the compound.
  • the substrate may be a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness, but is not limited thereto, and the substrate may be any substrate that is commonly used in organic solar cells. Specifically, there are glass or polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polypropylene (PP), polyimide (PI), and triacetyl cellulose (TAC). It is not limited to this.
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • PP polypropylene
  • PI polyimide
  • TAC triacetyl cellulose
  • the first electrode may be a transparent and excellent conductive material, but is not limited thereto.
  • Metals such as vanadium, chromium, copper, zinc and gold or alloys thereof;
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO);
  • Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb;
  • Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the method of forming the first electrode is not particularly limited, but may be applied to one surface of the substrate or in the form of a film using, for example, sputtering, E-beam, thermal deposition, spin coating, screen printing, inkjet printing, doctor blade or gravure printing. It can be formed by coating.
  • the first electrode When the first electrode is formed on the substrate, it may be subjected to cleaning, moisture removal, and hydrophilic modification.
  • the patterned ITO substrate is sequentially cleaned with a detergent, acetone, and isopropyl alcohol (IPA), and then 1 to 30 minutes at 100 ° C. to 150 ° C., preferably at 120 ° C. for 10 minutes on a heating plate to remove moisture.
  • IPA isopropyl alcohol
  • the surface of the substrate is modified to be hydrophilic.
  • the bonding surface potential can be maintained at a level suitable for the surface potential of the photoactive layer.
  • it is easy to form the polymer thin film on the first electrode during modification the quality of the thin film may be improved.
  • Pretreatment techniques for the first electrode include a) surface oxidation using parallel plate discharge, b) oxidation of the surface through ozone generated using UV ultraviolet light in a vacuum state, and c) generated by plasma. And oxidation using oxygen radicals.
  • One of the above methods can be selected according to the state of the first electrode or the substrate. In any case, however, it is preferable to prevent oxygen escape from the surface of the first electrode or the substrate and to minimize the residual of moisture and organic matter in common. At this time, the substantial effect of the pretreatment can be maximized.
  • a method of oxidizing a surface through ozone generated using UV may be used.
  • the patterned ITO substrate is baked on a hot plate and dried well, then put into a chamber, and a UV lamp is activated to cause oxygen gas to react with UV light.
  • the patterned ITO substrate can be cleaned.
  • the surface modification method of the patterned ITO substrate in this specification does not need to be specifically limited, Any method may be used as long as it is a method of oxidizing a substrate.
  • the second electrode may be a metal having a small work function, but is not limited thereto.
  • metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; LiF / Al, LiO 2 / Al, LiF / Fe, Al: Li, Al: BaF 2 , Al: BaF 2 It may be a material of a multi-layer structure such as, but is not limited thereto.
  • the second electrode is 5x10 - may be formed is deposited on the internal heat evaporator showing a degree of vacuum of less than 7 torr, not limited to this method.
  • the hole transport layer and / or electron transport layer material plays a role of efficiently transferring electrons and holes separated in the photoactive layer to the electrode, and the material is not particularly limited.
  • the hole transport layer material may be PEDOT: PSS (Poly (3,4-ethylenediocythiophene) doped with poly (styrenesulfonic acid)), molybdenum oxide (MoO x ); Vanadium oxide (V 2 O 5 ); Nickel oxide (NiO); Tungsten oxide (WO x ), and the like, but is not limited thereto.
  • PSS Poly (3,4-ethylenediocythiophene) doped with poly (styrenesulfonic acid)
  • MoO x molybdenum oxide
  • V 2 O 5 Vanadium oxide
  • NiO Nickel oxide
  • WO x Tungsten oxide
  • the electron transport layer material may be electron-extracting metal oxides, specifically, a metal complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Metal complexes including Liq; LiF; Ca; Titanium oxide (TiO x ); Zinc oxide (ZnO); And cesium carbonate (Cs 2 CO 3 ), and the like, but is not limited thereto.
  • metal oxides specifically, a metal complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Metal complexes including Liq; LiF; Ca; Titanium oxide (TiO x ); Zinc oxide (ZnO); And cesium carbonate (Cs 2 CO 3 ), and the like, but is not limited thereto.
  • the photoactive layer may be formed by dissolving a photoactive material, such as an electron donor and / or an electron acceptor, in an organic solvent and then spin coating, dip coating, screen printing, spray coating, doctor blade, brush painting, or the like. It is not limited to the method.
  • a photoactive material such as an electron donor and / or an electron acceptor
  • 3 is a diagram showing a result of NMR measurement of Compound C.
  • 5 is a diagram showing a result of NMR measurement of Compound D.
  • tris (dibenzylideneacetone) dipalladium (0) tris (dibenzylideneacetone) dipalladium (0), Pd 2 (dba) 3 ) (7.3mg, 0.008mmol) and tri (ortho-toryl) phosphine ( tri (o-tolyl) phosphine, P (o-tol) 3 ) (9.7mg, 0.032mmol) was added thereto, and stirred at 110 ° C for 72 hours. Then 0.5 mL of Br-benzotrifluoride was added and stirred at room temperature for 24 hours. The mixed solution was poured into chloroform, passed through a silica column, and the solvent was evaporated.
  • Compound 1 prepared in Preparation Example 1 was used as a donor, and PCBM was used as an acceptor to dissolve in chlorobenzene (Chlorobenzene, CB) in a 1: 2 ratio to prepare a composite solution.
  • CB chlorobenzene
  • the concentration was adjusted to 2.0 wt%
  • the organic solar cell was ITO / ZnO / photoactive layer / MoO 3 / Ag structure.
  • the glass substrate coated with ITO was ultrasonically cleaned using distilled water, acetone, and 2-propanol, ozonated the ITO surface for 10 minutes, and then heat-coated at 120 ° C. for 10 minutes by spin coating a ZnO precursor solution.
  • the composite solution was then filtered through a 0.45 ⁇ m PP syringe filter and then spin coated to form a photoactive layer. Thereafter, MoO 3 was deposited on the photoactive layer at a thickness of 5 nm to 20 nm at a rate of 0.4 dl / s in a thermal evaporator to prepare a hole transport layer. Thereafter, Ag was deposited at 10 nm on the hole transport layer at a rate of 1 dB / s in the thermal evaporator to manufacture an organic solar cell.
  • An organic solar cell was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 in Example 1.
  • An organic solar cell was manufactured in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in Example 1.
  • An organic solar cell was manufactured in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in Example 1.
  • An organic solar cell was manufactured in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1 in Example 1.
  • An organic solar cell was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1 in Example 1.
  • An organic solar cell was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1 in Example 1.
  • An organic solar cell was manufactured in the same manner as in Example 1, except that Compound 8 was used instead of Compound 1 in Example 1.
  • Example 1 0.793 3.87 0.35 1.09
  • Example 2 0.801 3.57 0.34 0.97
  • Example 3 0.800 3.36 0.44 1.18
  • Example 4 0.814 4.48 0.47 1.71
  • Example 5 0.815 4.36 0.47 1.67
  • Example 6 0.828 4.00 0.50 1.67
  • Example 7 0.805 13.603 0.571 6.26
  • Example 8 0.765 13.461 0.618 6.36
  • Voc denotes an open voltage
  • Jsc denotes a short circuit current
  • FF denotes a fill factor
  • ⁇ denotes an energy conversion efficiency.
  • the open-circuit and short-circuit currents are the X- and Y-axis intercepts in the four quadrants of the voltage-current density curve, respectively. The higher these two values, the higher the efficiency of the solar cell.
  • the fill factor is the area of the rectangle drawn inside the curve divided by the product of the short circuit current and the open voltage. By dividing these three values by the intensity of the emitted light, the energy conversion efficiency can be obtained, and higher values are preferable.

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